Natural Product: NPC474008

Natural Product ID:  NPC474008
Common Name:   Lupulin B
IUPAC Name:   [(1R,2S,4aR,5S,6R,8S,8aR)-5-[(2S,3aS,5R,6aR)-5-methoxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-8-acetyloxy-8a-(acetyloxymethyl)-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] (2R)-2-methylbutanoate
Synonyms:  
Molecular Formula:   C30H46O10
Standard InCHIKey:  KWASAXPCLHTNCZ-COFOGGAHSA-N
Standard InCHI:  InChI=1S/C30H46O10/c1-8-16(2)26(33)38-22-10-9-21-28(6,23-12-20-13-25(34-7)40-27(20)39-23)17(3)11-24(37-19(5)32)29(21,14-35-18(4)31)30(22)15-36-30/h16-17,20-25,27H,8-15H2,1-7H3/t16-,17-,20+,21-,22+,23+,24+,25-,27-,28+,29+,30-/m1/s1
Canonical SMILES:  CO[C@H]1C[C@H]2[C@@H](O1)O[C@@H](C2)[C@@]1(C)[C@H](C)C[C@@H]([C@@]2([C@@H]1CC[C@@H]([C@@]12CO1)OC(=O)[C@@H](CC)C)COC(=O)C)OC(=O)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO3534 Ajuga lupulina Species Lamiaceae Eukaryota PMID[8759163]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 1.2 mm 18625775
NPT19 Organism Escherichia coli Escherichia coli IZ = 1.2 mm 19075057

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC474008 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9302 High Similarity NPC475307
0.9286 High Similarity NPC470872
0.925 High Similarity NPC471216
0.925 High Similarity NPC471217
0.9136 High Similarity NPC71541
0.8929 High Similarity NPC235402
0.8889 High Similarity NPC266417
0.8837 High Similarity NPC221993
0.8588 High Similarity NPC18953
0.8506 High Similarity NPC213658
0.8506 High Similarity NPC45833
0.8506 High Similarity NPC62202
0.8506 High Similarity NPC110365
0.837 Intermediate Similarity NPC475765
0.828 Intermediate Similarity NPC113976
0.828 Intermediate Similarity NPC198549
0.8182 Intermediate Similarity NPC471411
0.8182 Intermediate Similarity NPC471410
0.8172 Intermediate Similarity NPC475785
0.8172 Intermediate Similarity NPC145553
0.8161 Intermediate Similarity NPC65133
0.8118 Intermediate Similarity NPC472943
0.8118 Intermediate Similarity NPC475456
0.8118 Intermediate Similarity NPC472951
0.8061 Intermediate Similarity NPC291414
0.8043 Intermediate Similarity NPC35164
0.8023 Intermediate Similarity NPC470154
0.8 Intermediate Similarity NPC292775
0.7935 Intermediate Similarity NPC475878
0.7931 Intermediate Similarity NPC470155
0.7931 Intermediate Similarity NPC477447
0.7931 Intermediate Similarity NPC477284
0.7931 Intermediate Similarity NPC477446
0.7907 Intermediate Similarity NPC186588
0.7872 Intermediate Similarity NPC21897
0.7857 Intermediate Similarity NPC107963
0.7849 Intermediate Similarity NPC122083
0.7849 Intermediate Similarity NPC256104
0.7849 Intermediate Similarity NPC12297
0.7849 Intermediate Similarity NPC182740
0.7849 Intermediate Similarity NPC211845
0.7841 Intermediate Similarity NPC213737
0.7841 Intermediate Similarity NPC474346
0.7841 Intermediate Similarity NPC474253
0.7841 Intermediate Similarity NPC474284
0.7841 Intermediate Similarity NPC475820
0.7826 Intermediate Similarity NPC470114
0.7816 Intermediate Similarity NPC470156
0.7802 Intermediate Similarity NPC471221
0.7802 Intermediate Similarity NPC476435
0.7791 Intermediate Similarity NPC477287
0.7789 Intermediate Similarity NPC252056
0.7789 Intermediate Similarity NPC203434
0.7789 Intermediate Similarity NPC237071
0.7789 Intermediate Similarity NPC238796
0.7778 Intermediate Similarity NPC268633
0.7766 Intermediate Similarity NPC191915
0.7766 Intermediate Similarity NPC151214
0.7745 Intermediate Similarity NPC86217
0.7732 Intermediate Similarity NPC470030
0.7727 Intermediate Similarity NPC208912
0.7727 Intermediate Similarity NPC216800
0.7727 Intermediate Similarity NPC2096
0.7711 Intermediate Similarity NPC123122
0.7701 Intermediate Similarity NPC134227
0.7701 Intermediate Similarity NPC186594
0.7684 Intermediate Similarity NPC57964
0.7684 Intermediate Similarity NPC94582
0.7677 Intermediate Similarity NPC139181
0.7677 Intermediate Similarity NPC476837
0.7677 Intermediate Similarity NPC97260
0.7653 Intermediate Similarity NPC476512
0.7653 Intermediate Similarity NPC472081
0.7653 Intermediate Similarity NPC108227
0.7647 Intermediate Similarity NPC305939
0.764 Intermediate Similarity NPC241959
0.7619 Intermediate Similarity NPC55508
0.7614 Intermediate Similarity NPC211049
0.7614 Intermediate Similarity NPC119922
0.7614 Intermediate Similarity NPC116320
0.7609 Intermediate Similarity NPC476379
0.7586 Intermediate Similarity NPC474754
0.7582 Intermediate Similarity NPC477283
0.7582 Intermediate Similarity NPC107603
0.7582 Intermediate Similarity NPC235196
0.7582 Intermediate Similarity NPC228593
0.7576 Intermediate Similarity NPC134967
0.7576 Intermediate Similarity NPC310138
0.7576 Intermediate Similarity NPC114700
0.7576 Intermediate Similarity NPC470029
0.7558 Intermediate Similarity NPC143250
0.7553 Intermediate Similarity NPC216137
0.7553 Intermediate Similarity NPC59006
0.7551 Intermediate Similarity NPC51579
0.7529 Intermediate Similarity NPC472950
0.7529 Intermediate Similarity NPC472952
0.7527 Intermediate Similarity NPC20822
0.7527 Intermediate Similarity NPC82955
0.7526 Intermediate Similarity NPC472273
0.7525 Intermediate Similarity NPC166079
0.7525 Intermediate Similarity NPC306776
0.75 Intermediate Similarity NPC60568
0.75 Intermediate Similarity NPC476718
0.7475 Intermediate Similarity NPC475574
0.7474 Intermediate Similarity NPC474379
0.7473 Intermediate Similarity NPC478111
0.7471 Intermediate Similarity NPC252483
0.7471 Intermediate Similarity NPC272841
0.7471 Intermediate Similarity NPC191345
0.7471 Intermediate Similarity NPC177343
0.7449 Intermediate Similarity NPC209798
0.7449 Intermediate Similarity NPC471374
0.7449 Intermediate Similarity NPC472144
0.7449 Intermediate Similarity NPC471375
0.7447 Intermediate Similarity NPC18536
0.7447 Intermediate Similarity NPC50443
0.7426 Intermediate Similarity NPC100078
0.7423 Intermediate Similarity NPC156377
0.7423 Intermediate Similarity NPC235109
0.7419 Intermediate Similarity NPC128475
0.7419 Intermediate Similarity NPC201607
0.7419 Intermediate Similarity NPC56777
0.74 Intermediate Similarity NPC244969
0.74 Intermediate Similarity NPC213528
0.7396 Intermediate Similarity NPC477224
0.7396 Intermediate Similarity NPC477495
0.7396 Intermediate Similarity NPC113500
0.7396 Intermediate Similarity NPC3538
0.7396 Intermediate Similarity NPC30687
0.7396 Intermediate Similarity NPC175
0.7391 Intermediate Similarity NPC477441
0.7391 Intermediate Similarity NPC215968
0.7391 Intermediate Similarity NPC131365
0.7391 Intermediate Similarity NPC155531
0.7374 Intermediate Similarity NPC471427
0.7374 Intermediate Similarity NPC471426
0.7374 Intermediate Similarity NPC471428
0.7368 Intermediate Similarity NPC5632
0.7368 Intermediate Similarity NPC229801
0.7368 Intermediate Similarity NPC473066
0.7368 Intermediate Similarity NPC307167
0.7368 Intermediate Similarity NPC210759
0.7368 Intermediate Similarity NPC149966
0.7363 Intermediate Similarity NPC471367
0.7363 Intermediate Similarity NPC79308
0.7347 Intermediate Similarity NPC472145
0.734 Intermediate Similarity NPC472234
0.734 Intermediate Similarity NPC472233
0.7333 Intermediate Similarity NPC286719
0.7333 Intermediate Similarity NPC477286
0.7327 Intermediate Similarity NPC34562
0.732 Intermediate Similarity NPC82633
0.732 Intermediate Similarity NPC473064
0.732 Intermediate Similarity NPC473065
0.732 Intermediate Similarity NPC215570
0.732 Intermediate Similarity NPC473067
0.7312 Intermediate Similarity NPC472396
0.7312 Intermediate Similarity NPC210658
0.7312 Intermediate Similarity NPC5943
0.7312 Intermediate Similarity NPC43912
0.7312 Intermediate Similarity NPC161928
0.7312 Intermediate Similarity NPC140446
0.7303 Intermediate Similarity NPC125366
0.73 Intermediate Similarity NPC475767
0.73 Intermediate Similarity NPC119467
0.73 Intermediate Similarity NPC476838
0.73 Intermediate Similarity NPC476839
0.7294 Intermediate Similarity NPC109510
0.7292 Intermediate Similarity NPC311246
0.7292 Intermediate Similarity NPC167644
0.729 Intermediate Similarity NPC79193
0.7283 Intermediate Similarity NPC477445
0.7283 Intermediate Similarity NPC290612
0.7282 Intermediate Similarity NPC126753
0.7273 Intermediate Similarity NPC43463
0.7264 Intermediate Similarity NPC477489
0.7263 Intermediate Similarity NPC473542
0.7263 Intermediate Similarity NPC471371
0.7263 Intermediate Similarity NPC471370
0.7253 Intermediate Similarity NPC30102
0.7253 Intermediate Similarity NPC111582
0.7253 Intermediate Similarity NPC477285
0.7253 Intermediate Similarity NPC128816
0.7253 Intermediate Similarity NPC67158
0.7245 Intermediate Similarity NPC142264
0.7245 Intermediate Similarity NPC296936
0.7245 Intermediate Similarity NPC476510
0.7245 Intermediate Similarity NPC163685
0.7241 Intermediate Similarity NPC136424
0.7228 Intermediate Similarity NPC80640
0.7222 Intermediate Similarity NPC243981
0.7222 Intermediate Similarity NPC190940
0.7216 Intermediate Similarity NPC45959
0.7216 Intermediate Similarity NPC252253
0.7216 Intermediate Similarity NPC305418
0.7212 Intermediate Similarity NPC207693
0.7209 Intermediate Similarity NPC166250
0.7209 Intermediate Similarity NPC308489
0.7204 Intermediate Similarity NPC114378
0.7204 Intermediate Similarity NPC64862

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC474008 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7253 Intermediate Similarity NPD3669 Approved
0.7253 Intermediate Similarity NPD3670 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD1780 Approved
0.7033 Intermediate Similarity NPD1779 Approved
0.6939 Remote Similarity NPD8171 Discontinued
0.6923 Remote Similarity NPD8170 Clinical (unspecified phase)
0.686 Remote Similarity NPD2254 Approved
0.686 Remote Similarity NPD2686 Approved
0.686 Remote Similarity NPD2687 Approved
0.6822 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6796 Remote Similarity NPD1700 Approved
0.6667 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6636 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6577 Remote Similarity NPD8133 Approved
0.6559 Remote Similarity NPD6928 Phase 2
0.6522 Remote Similarity NPD6697 Approved
0.6522 Remote Similarity NPD6115 Approved
0.6522 Remote Similarity NPD6118 Approved
0.6522 Remote Similarity NPD6114 Approved
0.6455 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6444 Remote Similarity NPD1811 Approved
0.6444 Remote Similarity NPD1810 Approved
0.6435 Remote Similarity NPD7516 Approved
0.6413 Remote Similarity NPD6116 Phase 1
0.6364 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6348 Remote Similarity NPD7327 Approved
0.6348 Remote Similarity NPD7328 Approved
0.6304 Remote Similarity NPD6117 Approved
0.6273 Remote Similarity NPD6686 Approved
0.6261 Remote Similarity NPD8295 Clinical (unspecified phase)
0.625 Remote Similarity NPD7507 Approved
0.6239 Remote Similarity NPD6008 Approved
0.6239 Remote Similarity NPD8294 Approved
0.6239 Remote Similarity NPD8377 Approved
0.6222 Remote Similarity NPD5777 Approved
0.6198 Remote Similarity NPD8293 Discontinued
0.6186 Remote Similarity NPD8033 Approved
0.6186 Remote Similarity NPD8296 Approved
0.6186 Remote Similarity NPD8335 Approved
0.6186 Remote Similarity NPD8380 Approved
0.6186 Remote Similarity NPD8379 Approved
0.6186 Remote Similarity NPD8378 Approved
0.6174 Remote Similarity NPD6940 Discontinued
0.6148 Remote Similarity NPD7736 Approved
0.6134 Remote Similarity NPD6370 Approved
0.6126 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6098 Remote Similarity NPD7319 Approved
0.6087 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6067 Remote Similarity NPD229 Approved
0.6036 Remote Similarity NPD6412 Phase 2
0.6033 Remote Similarity NPD7492 Approved
0.6 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5984 Remote Similarity NPD6616 Approved
0.5977 Remote Similarity NPD371 Approved
0.5966 Remote Similarity NPD6054 Approved
0.5966 Remote Similarity NPD6059 Approved
0.595 Remote Similarity NPD8328 Phase 3
0.5935 Remote Similarity NPD7078 Approved
0.5917 Remote Similarity NPD7503 Approved
0.5865 Remote Similarity NPD8035 Phase 2
0.5865 Remote Similarity NPD8034 Phase 2
0.5851 Remote Similarity NPD3702 Approved
0.5851 Remote Similarity NPD3703 Phase 2
0.5849 Remote Similarity NPD7991 Discontinued
0.5833 Remote Similarity NPD7638 Approved
0.582 Remote Similarity NPD6067 Discontinued
0.5818 Remote Similarity NPD8301 Approved
0.5818 Remote Similarity NPD8300 Approved
0.5785 Remote Similarity NPD6015 Approved
0.5785 Remote Similarity NPD6016 Approved
0.578 Remote Similarity NPD7640 Approved
0.578 Remote Similarity NPD7639 Approved
0.5776 Remote Similarity NPD6882 Approved
0.5738 Remote Similarity NPD5988 Approved
0.573 Remote Similarity NPD9496 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6009 Approved
0.5701 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5699 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5699 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5688 Remote Similarity NPD4225 Approved
0.5676 Remote Similarity NPD7632 Discontinued
0.5656 Remote Similarity NPD6921 Approved
0.5652 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5652 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5641 Remote Similarity NPD8297 Approved
0.5636 Remote Similarity NPD6648 Approved
0.5619 Remote Similarity NPD3168 Discontinued
0.5607 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5607 Remote Similarity NPD7900 Approved

Structure

External Identifiers

PubChem CID   44566823
ChEMBL   CHEMBL458054
ZINC  

Physicochemical Properties

Molecular Weight:  566.31
ALogP:  -1.0684
MLogP:  3.66
XLogP:  4.049
# Rotatable Bonds:  18
Polar Surface Area:  119.12
# H-Bond Aceptor:  10
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  40

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs